A ru-catalyzed four-component coupling [6]

Journal of the American Chemical Society

Volumn 122, Issue 33, 2000, Pages 8081-8082

  Trost, Barry M ^a   Pinkerton, Anthony B ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

RUTHENIUM DERIVATIVE;

ALKYLATION; BINDING SITE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; LETTER; PROTON TRANSPORT; REACTION ANALYSIS; SPECTROSCOPY; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 0034706016     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001656v     Document Type: Letter

References (28)

1. For a lead reference on the Ugi reaction, see: Ugi, I. J. Prakt. Chem. 1997, 339, 499. Also: Ugi, I.; Lohberger, S.; Karl, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1999; Vol. 2, Chapter 4.6.
2. For a lead reference on the Ugi reaction, see: Ugi, I. J. Prakt. Chem. 1997, 339, 499. Also: Ugi, I.; Lohberger, S.; Karl, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1999; Vol. 2, Chapter 4.6.
3. For some examples of the Ugi reaction and other multicomponent reactions in combinatorial chemistry, see: Domling, A. Combinatorial Chem., High Throughput Screening 1998, 1, 1. Kobayashi, S. Chem. Soc. Rev. 1999, 28, 1.
4. For some examples of the Ugi reaction and other multicomponent reactions in combinatorial chemistry, see: Domling, A. Combinatorial Chem., High Throughput Screening 1998, 1, 1. Kobayashi, S. Chem. Soc. Rev. 1999, 28, 1.
5. Trost, B. M. Science 1991, 254, 1471.
6. (a) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 1988.
7. (b) Trost, B. M.; Pinkerton, A. B. Angew. Chem., Int. Ed. 2000, 39, 360.
8. (a) For some examples of Ru enolates, see: Hartwig, J. F.; Bergman, R. G.; Anderson, R. A. Organometallics 1991, 10, 3326. Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852.
9. (a) For some examples of Ru enolates, see: Hartwig, J. F.; Bergman, R. G.; Anderson, R. A. Organometallics 1991, 10, 3326. Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852.
10. (b) For some examples of metal-catalyzed addition to Michael acceptors followed by aldol reactions, see: Taylor, S. J.; Morken, J. P. J. Am. Chem. Soc. 1999, 121, 12202. Kiyooka, S.; Shimizu, A.; Torri, S. Tetrahedron Lett. 1998, 39, 5237. Matsuda, I.; Takahashi, K.; Sato, S. Tetrahedron Lett. 1990, 31, 5331. Revis, A.; Hilty, T. Tetrahedron Lett. 1987, 28, 4809.
11. (b) For some examples of metal-catalyzed addition to Michael acceptors followed by aldol reactions, see: Taylor, S. J.; Morken, J. P. J. Am. Chem. Soc. 1999, 121, 12202. Kiyooka, S.; Shimizu, A.; Torri, S. Tetrahedron Lett. 1998, 39, 5237. Matsuda, I.; Takahashi, K.; Sato, S. Tetrahedron Lett. 1990, 31, 5331. Revis, A.; Hilty, T. Tetrahedron Lett. 1987, 28, 4809.
12. (b) For some examples of metal-catalyzed addition to Michael acceptors followed by aldol reactions, see: Taylor, S. J.; Morken, J. P. J. Am. Chem. Soc. 1999, 121, 12202. Kiyooka, S.; Shimizu, A.; Torri, S. Tetrahedron Lett. 1998, 39, 5237. Matsuda, I.; Takahashi, K.; Sato, S. Tetrahedron Lett. 1990, 31, 5331. Revis, A.; Hilty, T. Tetrahedron Lett. 1987, 28, 4809.
13. (b) For some examples of metal-catalyzed addition to Michael acceptors followed by aldol reactions, see: Taylor, S. J.; Morken, J. P. J. Am. Chem. Soc. 1999, 121, 12202. Kiyooka, S.; Shimizu, A.; Torri, S. Tetrahedron Lett. 1998, 39, 5237. Matsuda, I.; Takahashi, K.; Sato, S. Tetrahedron Lett. 1990, 31, 5331. Revis, A.; Hilty, T. Tetrahedron Lett. 1987, 28, 4809.
14. For an example of a Ru-catalyzed addition to a Michael acceptor, sec: Yi, C. S.; Liu, N. J. Organomet. Chem. 1998, 553, 157.
15. For a recent example, see: Loh, T. P.; Zhou, J. R. Tetrahedron Lett. 1999, 40, 9115.
16. All new compounds have been characterized spectroscopically, and elemental composition has been established by combustion analysis or high-resolution mass spectroscopy.
17. Trost, B. M.; Indolese, A.; Müller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615.
18. For an overview of the aldol reaction, see: Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, Chapters 1.5 and 1.6.
19. For generation and use of rhodium enolates in aldol reactions, sec: Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938. Reetz, M. T.; Vougioukas, A. E. Tetrahedron Lett. 1987, 28, 793. Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517. For Pd and Pt, see: Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032. Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc: 1998, 120, 2747. Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
20. For generation and use of rhodium enolates in aldol reactions, sec: Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938. Reetz, M. T.; Vougioukas, A. E. Tetrahedron Lett. 1987, 28, 793. Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517. For Pd and Pt, see: Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032. Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc: 1998, 120, 2747. Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
21. For generation and use of rhodium enolates in aldol reactions, sec: Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938. Reetz, M. T.; Vougioukas, A. E. Tetrahedron Lett. 1987, 28, 793. Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517. For Pd and Pt, see: Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032. Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc: 1998, 120, 2747. Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
22. For generation and use of rhodium enolates in aldol reactions, sec: Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938. Reetz, M. T.; Vougioukas, A. E. Tetrahedron Lett. 1987, 28, 793. Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517. For Pd and Pt, see: Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032. Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc: 1998, 120, 2747. Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
23. For generation and use of rhodium enolates in aldol reactions, sec: Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938. Reetz, M. T.; Vougioukas, A. E. Tetrahedron Lett. 1987, 28, 793. Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517. For Pd and Pt, see: Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032. Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc: 1998, 120, 2747. Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
24. For generation and use of rhodium enolates in aldol reactions, sec: Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938. Reetz, M. T.; Vougioukas, A. E. Tetrahedron Lett. 1987, 28, 793. Sato, S.; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517. For Pd and Pt, see: Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032. Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc: 1998, 120, 2747. Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
25. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
26. See Supporting Information. A similar procedure giving the same relative stereochemistry was peformed for the product (14) from entry 3, Table 1.
27. Transmetalation of the Ru enolate to form a tin enolate prior to the aldol reaction cannot be ruled out.
28. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920.